Accidentally Samantha
My girlfriend and I were at the Dock in Keywest for a
Snorkeling trip when Jennifer suddenly started complaining about how
her stomach was bothering her. This was no surprise Jennifer never
wanted to do anything but this time I thought she might go. She said
"You go I don't want to spoil your fun ." What could I do, I went, As
the 60 foot Catamaran pulled away from the pier she waved then headed
back to the hotel.
I am about 28, 5'7" long Dirty Blond hair usually kept in a
pony tail, Slightly overweight but not fat. I have been teased about
my physic since I was a child. Wide hips skinny waist and heavy in the
chest area so much so that the other guys always tell me I need a
bra. And practically no body hair, Let me rephrase that. Thanks to
Jennifer, No body hair. Yesterday we were over to Fort Monroe beach
sunbathing when Jennifer decided that I was starting to burn and I
needed Sunblock so she pulled out her bottle and totally rubbed me
down with the lotion, Jennifer is one of those people who take things
out of there original containers and put it in her own designer
containers. Sun block is no exception. After about 5 minutes I felt a
burning sensation and decided it was time to go into the water. As I
entered the water all of my body hair just rinsed away. It was a good
thing I stuffed the hair on my head up under my hat. My leg hair, My
chest hair even the hair under my arms just rinsed away. I came back
in and asked Jennifer what was in the bottle she took the top off and
smelled it and giggling told me she had accidentally grabbed the
bottle of Nair. She then had the giggles for most of the day. I was
pissed off but that night she kept running her hands over me telling
me how much my smooth skin turned her on, I do have very smooth and
fair skin. We had the best sex we ever had.
Back to the Sail boat, On a snorkeling trip they sail you out to the
coral reef for an hour then you have an hour of swimming and diving
then you sail back, On the way back they provide you with all the beer
and wine you can drink. It was a beautiful day the sun was shinning
there was enough wind that the Catamaran was sailing at a nice clip. I
had removed my shirt and was sitting with two middle aged couples, We
were engaged in some nice conversation when a gust of wind took my Tee
Shirt over the side. It was a nice day so I did not care and moved up
front. When we finally arrived at the Reef I was more than happy to
get in the water the swimming was wonderful I saw giant schools of
parrot fish, Barracuda, Coral heads. All at once the waves and the
wind kicked up a little. And we were asked to return to the boat. In
the middle of the boat they drop a stairway down. You swim up and take
off your swim fins and then climb on to the stairway then walk up on
to the deck, That is what you are supposed to do, What I did was take
off my fins and try to step on to the stairway when the boat shifted
and the stairway moved in such a way that it totally ripped off my
bathing suit which then sank like a rock. What was I to do, I covered
myself with the swimfins and made my way to my beach bag as the crew
giggled at me I looked into my beach bag hoping that Jennifer had
packed me and extra pair of shorts. Much to my dismay all I found was
a Postage Stamp size towel and one of Jennifer's frilly
sundresses. While trying to cover myself with the fins I tried to
arrange the towel in a concealing manner. Finally I gave up and
decided to try on the sundress as I unfolded it and looked on a floral
print that was beige and white with two rows of white lace around the
bottom and another row around the top and two straps that went over
the shoulders. The lady sitting closest to me said she thought I would
look very pretty in it and they all laughed. I thought what the hell
and pulled it over my head to my surprise it fit perfectly, To
perfectly, Just below the breasts was an elastic that acted like a bra
pulling breasts up and out. From there it hugged me finally flaring
out with my hips dropping in a very feminine flattering manner. I
pulled my pony tail out from the back and stood up to pull it down and
felt my breasts being shaped in a manner I was not used to. The hem
line hung down and I felt the lace caressing my thighs. I looked down
thinking how much it turned me on when Jennifer wore this dress and
started to get quite aroused and sat back down. The Couples near me
were just staring at me. The lady who had heckled me earlier Said "I
told you that you would look very pretty in it". Only there was a
different tone in her voice the others just nodded. Just then one of
the crew came by giving out beer and wine. When he came to me I could
see that he did not recognize me as the one who had lost his bathing
suit. What he did do was look me up and down and say "Darling what can
I get for you". I said "beer" he responded "If I can get you anything
else just holler and walked off to serve the others. The lady next to
me said "He did not treat us like that". I blushed and decided that I
would take my brush and go up on the front to dry my hair and drink my
beer. I got up front and undid my pony tail and started brushing out
the hair. I do get lots of compliments on my hair, Jennifer once told
me if I cut my hair she will break up with me, She don't have to
worry. I started to brush it out.
I was standing up against the railing and my hair was dry in no time,
With the salt water and the sun and the breeze it dried very soft and
flowing. So I stood there with my hair tickling my shoulders in the
breeze and the lace tickling my thighs just watching across the boat
at the beautiful water and sky when this guy walked up on the other
side of the boat and smiled at me. I smiled back not really thinking
anything when he raised his camera and took my picture. I was
surprised not really comprehending when I looked back and noticed I
had drawn Quite a few male eye's looking at me in a way that no male
had ever looked at me before. I thought, they must know I am a guy
after half the boat had seen my parts and the other half saw me put on
the dress and I could not look like a girl. I looked down and saw a
very pretty dress, Long slender hairless legs and long blond hair
flowing in the wind. And thought these guys are strong swimmers and
would still have been in the water looking at the fish and would not
have witnessed my depanting, One look back at them and I decided, Yes
they do think I am a girl and they want me. Even the guys who were
sitting there and knew were looking at a guy. I was embarrassed and
looked around and yes a few of them seemed to be aroused. I had
dressed as a girl for Halloween before with some success, I had worn
my mothers old bathrobe and bathing cap, It was fun. I have also seen
pretty girls wearing pretty dresses and fantasized about dressing up
like that and flirting with guys wondering how the clothes would feel,
But that was just fantasy. I was startled out of my reverie by another
guy with a camera, This one the boat photographer the same guy who had
served me beer earlier. He said "Excuse me beautiful but could you
take just two steps back" He looked in the camera and said "OK now
look into the wind, Perfect" he took the picture. Stepped closer and
said "That is prettiest picture I have taken all week, Can I have your
name" I was horrified and said "Sam". He said "Glad to meet you, your
picture will be available one hour after we land at the dock you
should come look, Your very pretty". As he left I looked toward the
other side of the boat and saw we were starting to get near
shore. There were three guys and two girls standing there. The two
girls were wearing bikini's and looked away when I caught them
staring. The guy in the middle who looked to me to be the unattached
one. Borrowed the camera from one of his buddies and walked towards me
asked if I would smile for him, I had no choice I also blushed. He
then snapped the picture. He also asked if one of his buddies could
take a picture of him with me. He did not wait for an answer and
walked up and put his arm around me and kissed me full on the lips as
his buddy snapped the picture. I was ready to punch him when he got on
his knees in front of me and begged for forgiveness and kissed my
hand. He then offered to buy me a drink. I was laughing as were his
friends by this time and told him that the drinks were free. He said
"That's OK I will buy it for you if that will make you happy". I
decided to play along for a while then tell him of his error to
embarrass him in front of his friends besides much to my surprise I
decided that he was cute. He had the body that I always wished I had,
Broad shoulders and a skinny waist and a big happy smile, If I were a
girl I would think he was Cute. He returned with my drink and said
"That was expensive, But well worth it. Did anyone ever tell you that
you are beautiful ? And are you here with anyone ?" I replied " I am
not on the cruise with anyone, But my girlfriend is back at the hotel
room." This cheered him up a bit as he inquired " Would you go to
dinner with me after the cruise, And depending on how dinner goes out
for a drink after that and depending on how the drink goes maybe back
to my place for a nightcap and maybe to spend the night and possibly
the rest of your life ?" I said " I guess you believe in love at first
sight, You don't know anything about me, Maybe I have a Deep dark
secret that will scare you away." He replied "How could anyone as cute
as you have done anything evil ?" I responded "I did not say evil, I
just said deep and Dark." Just then a breeze came up that almost
exposed me for what I was, I then realized this was my fantasy, I was
dressed as a pretty girl flirting with a cute guy. He then said " My
name is Dave and I have to tell you I have been looking for a girl
like you all my life you are a perfect 10 in my book so tell me your
secret and then marry me". So I told him" I can tell you my secret,
But I cannot marry you. My secret is that when I came aboard the
cruise earlier I was a boy". Dave responded "A boy ?" I said "Yes a
boy, Or let me rephrase that, A male." Dave said "That's impossible. I
need proof." I said "Proof I have, There is always the Crocodile
Dundee test." Dave said " I am not quite ready for that yet, But How
did you arrive as a boy and end up as the girl I now see in front of
me ? Inquiring minds want to know." I related to him the Lost the
bathing suit, Girlfriends sundress story, Finishing up by saying that
I moved up on the bow to comb my hair because they were embarrassing
me below. When suddenly all the males started taking my picture and
wanting to marry me. Dave asked " why are your legs and chest shaved
?" So I told him about the Nair incident at the beach the day before.
Dave responded "So your telling me you have never dressed as a girl
before and you accidentally ended on the front of a sailboat looking
like a centerfold ?" I said " I might have phrased it differently but
yes." Dave looked me up and down shook his head and said " You are
still one of the prettiest girls I have ever seen, Knowing you are
actually a guy turns me on even more, I am not gay and have never been
with a guy before but I want you, Would you still have dinner with me
?" I told him I was very flattered but all the money I had went down
with my shorts. And I wanted to change." Dave smiled at this and
replied "Dinner is on me and I do not want you to change I love you
just the way you are." I felt his hand move over and grab my butt. His
friends were looking on and winking at him. Dave leaned close and
whispered in my ear "if only they knew" I suddenly thought what would
Jennifer and everyone else think if they knew I was making a date to
go out dressed as a girl. I dismissed the thought thinking this is
just to much fun this is the stuff fantasy's are made out of.
The boat docked, Dave insisted on carrying my beach bag. We
made our way down Caroline St. the Jimmy Buffet song Woman going Crazy
on Caroline St. Ran Through my mind. We walked past Sloppy Joes up on
to Duval St. I stopped and called Jennifer and told her that I was
going out for a drink with one of the guys I had meet on the
boat. Dave said he wanted to take me to Blue Heaven for dinner. We
were about to pass a store when Dave suddenly grabbed my arm and
pulled me into the store and there in front of me was a full length
mirror. The guy I recognized but the pretty blond girl standing next
to him in the frilly dress had my face but could not be me ! I moved
my hand up to touch my face and the Pretty girl moved her hand up at
the same time. I now understood Dave and the other guys reaction, Why
I would have gone after me. Dave who had been watching intently said "
I now believe you, That reaction could not have been faked and yes you
do look like a wet dream." We turned around to find we were in a
lingerie shop I looked at the stuff and Blushed, I could not believe
what I was thinking I was getting horny thinking about wearing this
stuff. Dave pulled me over to a table and lifted up this virginal
white skimpy nighty and held it up to me and said "You would look hot
in this. By the way if you don't mind my asking what type of Panties
are you wearing as he started to tug at the hem of my dress. I told
him that all I had was the dress I had nothing on under it. Dave
steered me over to a rack and said "A pretty girl like you needs sexy
underwear. He picked up a white pair of lacy panties that looked like
they would fit and said "how about these ? " I blushed and said "I
have no money." Dave responded " I do, This is the most fun I have had
in years allow me to buy them for you." A sales girl walked over and
Dave asked her "I want these and a matching bra. " I blushed again "
The girl turned to me and asked what size." I responded " Uh, I don't
know ." Dave smiled and laughed. The sales girl said if you will allow
me and she pulled out a tape measure and proceeded to take chest
measurements in the process managing to totally feel my breasts
up. She finally announced, A thirty six C. I was amazed. She then went
to a rack and produced a very frilly white bra that matched the
panties. Dave nodded his approval and said "Why don't you try them
on.?" the girl pointed to the dressing room in the back and asked if I
needed assistance, I declined the assistance and proceeded back I was
quite turned on by the whole thing and I did not want the girl to
see. Dave said" If they fit good just leave them on. I closed the door
and took off the dress. I looked at the mirror as I pulled up the
panties, They felt wonderful as I tucked my parts away. The bra I put
on backward as I had seen my Girlfriend do and turned it around I put
the straps on and adjusted them and pulled my breasts up into the
cups, It felt very natural and comfortable as sexy and silky. I looked
in the mirror and could not believe the feminine aspect I had
assumed. I heard Dave outside say " Can we see ?" I told him, later. I
pulled the dress back on. The Bra made the dress look even more
Feminine and the panties helped to hide that tell tale bulge. I
stepped back out Dave looked on with hungry eye's he passed me some
sandals with heels on them and said try these. They fit perfectly as
every other thing had today. The sales girl walked over and said Dave
explained the situation and you look awesome. If you don't mind I want
to try some makeup on you. I agreed, She used a little Eye liner and
some lipstick and a little blush.
We all turned and looked in the mirror, The illusion was complete. To
all appearances I was not only a girl but a very nice looking one. I
said Why can't I get girls that look as good as I do to go out with me
? The sales girl was looking at me with the same hungry eye's that
Dave was. She informed me " I will go out with you, You turn me on
more that you can imagine." She gave me her business card and said
call me. I was a little unsteady on the heels at first but soon got
used to them. All the guys were staring at me especially the ones with
girl friends. Dave grabbed my hand an I moved over next to him and he
put his arm around me to steady me. I found I liked this. He said " Do
you realize how easily you have fallen into the feminine roll ? I
really do feel like I am walking down the street with my girl friend."
He then moved his hand down and caressed my bottom.
I thought if a guy had done that yesterday I would have smacked him,
Or would I have ? We reached Blue Heaven and took a seat out side Dave
sat next to me and ordered. With all the chickens running around I was
glad he did not order Chicken. We sat and talked and had a few
beers. After a few minuets I felt Dave rest his hand on my leg. He
commented "You have such smooth skin are you sure your not a girl ?" I
said " At this moment I am not sure." He moved his hand higher up
under my dress caressing my thigh, Finally he reached his target. He
looked at me and raised one Eyebrow in a Spock like fashion and said
"Fascinating!" As he caressed me through the silken panty material. I
thought I would cream right then. At this moment the waiter brought
our food and Dave removed his hand from the forbidden zone. As we ate
Dave said "You don't know how turned on I am." I said "You do know how
turned on I am." For the first time all night Dave blushed. I leaned
over to him strategically placing my hand on his lap and kissed him on
the lips while grabbing a handful and yes Dave was as excited as I
was.
We walked back over to Duval St. And went to Captain Tony's I ordered
a Pirates Punch and we sat down to watch the band. David's friends
showed up, One of them had stopped and picked up our pictures unknown
to me at David's request. We looked at them, I could understand why
Dave had thought I was a girl. After a while we got up and danced,
Some things are easy being a girl dancing in heels is not one. It took
a while to get used to the heels as well as getting used to not
leading. I got the hang of it soon. Dave was groping me all over
. Eventually we were up near the bar I was leaning back against Dave,
He had his arms around my front holding my tits I could feel him
pushing my dress between my legs when he leaned down and pulled my
hair back and nibbled my earlobe and suggested we adjourn back to his
room for a nightcap.